


Kinky Winchesters

by Cagedandfree



Series: Good boys for Dean [2]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, Bottom Sam, Butt Plugs, Caring Dean, Cock Cages, Cock Warming, Comfort, Crossdressing, Crossdressing Sam Winchester, Daddy Issues, Daddy Kink, Feminization, I'll add more when I think, Light Dom/sub, M/M, Panty Kink, Pet Names, Praise Kink, Sam In Panties, Sam in bright red lipstick, Sam wants to be Dean's good girl, Top Dean, Wincest - Freeform
Language: English
Status: Completed
Published: 2018-01-09
Updated: 2018-01-09
Packaged: 2019-03-02 13:30:59
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 3,899
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13319151
Author URL: https://archiveofourown.org/users/Cagedandfree/pseuds/Cagedandfree
Summary: Learning of Dean and Castiel's kinks. Sam tells Dean his and Dean is happy to help his brother out.Sequel to Kinky Destiel.





	1. Chapter 1

**Author's Note:**

> This is Sam and Dean's story, not much Castiel.

Dean asked Castiel if he would be comfortable having Sam come and play with them. 

“Would he drink…”Castiel trailed off. 

“No baby.” Dean said kissing Castiel. “He will not take part in that. That is only for us. No, Sam has a different kink.” Castiel nodded.

“What is it?” 

“Before I tell you, I need to make sure Sam is okay with that.”

“I understand.”

“Now, you have some bottles ready for you, but I will spending the weekend with Sam.” Castile smiled wanting to know what Sam’s thing was. 

“Dean, will…I…be able.” Castiel paused.

“What is it?” Dean soothed, pulling the older man close to him.

“Do I have to fill up bottles?” Castiel whispered. 

“No. You finish what we have in the fringe, I labelled them. Since I wont be around, I think it’s only fair that you have coffee, whenever you want.” Dean kissed the top of his head and Castiel hugged him tight.

Dean drove to the motel where the younger Winchester was waiting. One drunk night a few weeks ago, they were talking about kinks and Dean told Sam what he and Castiel do. Sam did not judge. Dean asked Sam, who hesitated, but finally told Dean. 

“Really?” Dean said raising an eyebrow.

“Uh..yeah. God, I’m a freak.” Sam covered his face.

“Sammy, I just told you that Castiel is basically my human urinal. You are not a freak.” 

“I wanted to be sort of want to try it, with someone, but I don’t know who.”

“I’ll do it.” Dean offered.

“What? Seriously?!” Sam looked at his brother skeptical.

“Well, wouldn’t you be more comfortable with someone you knew?” 

“Yeah…sure…but you’re my brother.”

“Hey, I was just offering” Dean said, trying to put the younger man at ease. 

“…. Would you…” Sam asked looking done. Dean placed a hand on his brothers knee.

“Just tell me when. Let me talk to Castiel, if he gives the okay, then I’m in.”

“But…please, don’t tell him…not yet” Sam said.

“I wont. I’ll just let him know that you have a kink, that requires a bit of dominance and that if it was okay, you would like me to be your Dom.”

Dean pulled into the motel parking lot. Sam texted him the number. Dean knocked and Sam opened the door, letting Dean in. The blinds were already closed and there was a do not disturb sign on the door.

“Are you ready?” Dean smiled and Sam blushed.

“Yes, Dean.” Sam answered.

“Castiel is very excited to learn what we are doing. I didn’t tell him of course. Just what I told you I would say.” Sam sighed in relief.

“Okay Sammy, do you have the stuff?” Dean asked.

“Ye-yes” Sam’s heart started to race. Dean cupped his brother’s cheek.

“You’re okay. There is no judgment here. You’re in a safe place.”

“I know, just never really done this.” Dean smiled a bit.

“We’ll take it nice and slow.” Sam nodded. 

“I’m ready.” He said.

“You sure?” Dean asked and Sam looked up at him with puppy dog eyes.

“Yes.”

“Okay.” Dean stroked his brothers hair. “Sammy, you going to show me how pretty you are?” 

“Yes, Dean” he whispered.

“Good boy. Go show me how pretty you are.”

Sam took a deep breath and walked into the bathroom. A few minutes later the bathroom door opened and Dean stood their looking at his brother.

Sam was wearing black satin panties, thigh high fishnets and high heels, nothing else. Dean scanned his brothers body and had Sam turn around.

“Bend over, sweetheart” Dean commanded gently.

Sam did and Dean pulled the paints aside to see a black silicon plug in Sam’s ass. He moved the panties back and Sam stood straight and turned to face Dean.

“Dean, do you think I’m pretty?” Sam asked timidly.

“Yes, princess, I think you’re very pretty” Dean smiled.


	2. Chapter 2

Dean reached up and stroked his brother’s cheek.

“Dance for me, sweetheart.”

“Hmm.” Sam swallowed.

“I’m going to sit on the bed and you’re going to put on a little show for me. If you get nervous, close your eyes and pretend you’re alone” He whispered in Sam’s ear.

“Yes, Dean” Sam whispered.

Dean sat on the bed and watched as his brother swayed his hips side to side. Sam closed his eyes and lightly touched his own cheek. He slowly got into it, completely forgetting where he was. He moaned and started to turn, swaying side to side.

When he remembered the Dean was there, Sam turned around and blushed. Dean reached out a hand and Sam took it. Dean guided Sam to stand between his legs. Dean ran his hands up and down Sam’s sides.

“So beautiful, sweetheart.” Dean said and Sam looked away and blushed. Dean stood up and turned Sam’s chin to make him look Dean in the eyes. “You look so beautiful like this, Sammy. Are you my pretty boy?” he murmured, lightly placing a kiss on Sam’s lips.

“Ye-yes, Dean” Sam stammered. Dean kissed him gently again.

“Thank you for dancing for me.” 

“You’re welcome” Sam said breathlessly. Dean ran a finger along the edge of the satin panties and Sam gasped.

“You like dressing up in these black panties? You like getting all pretty?”

“Yes.” Sam whimpered.

“I have something else I would like you to try, but we wont do that tonight.” Dean said stroking Sam’s cheek. 

“Okay.” 

“I have some research to do. Can you do me a favor?” Sam nodded. “I want you to kneel under the table and warm my cock. Can you do that for me, princess?” Dean asked running a hand through the younger man’s hair. 

“Yes.”

“Can you beg, sweetheart?”

“Please Dean. Please, let me warm your cock, I want to be put to good use. I want to be your good boy.”  
“My pretty princess?” Dean asked and Sam gulped. “Say “it.”

“I want to be your pretty princess” Sam begged. Dean smiled sweetly and deeply kissed his Sam. 

“If that’s what you want, Sweetheart. You can be my pretty princess.” 

An hour later, Dean looked at the clock and reached down, running a hand through Sam’s hair.

“Good job. Good boy. Come on out.” Dean praised. Sam crawled out and stood up. 

Dean was completely naked. He led Sam over to the bed and sat Sam down, running his hands through his long hair.

“What a good job you did Sweetheart. My cock was all nice and warm. Now, I’m going to get you out of this and put you cock in the cage once you’re ready for bed.”

“Yes Dean.” Sam said.

Dean had Sam lay back and he lifted his leg and took of his heel and he did the same with the other foot. Dean pulled the fishnets off and the satin panties. Dean had Sam lift and bend his legs. Dean placed latex gloves on and pulled the plug out. 

Sam went to the bathroom and brushed his teeth while Dean got ready for tomorrow. Dean put latex gloves on again and caged Sam’s cock. He tucked his younger brother in and then went to hand wash the panties. 

Sam was a good boy. A pretty princess for his big brother and Dean couldn’t wait to show him, what he had planned tomorrow. He crept to bed and slid in next to his brother and held him close, placing a kiss on the back of his head.


	3. Chapter 3

In the morning, Dean took the cage off of Sam and Sam went to the bathroom and Dean walked in, wrapping his arms around the younger man’s waist.

“Sammy, I want you to put your plug in and your panties on, but you’re going to put your fishnet stockings and heels on in front of me.”

“Yes Dean.” Sam said.

“Are you sure you’re ready to go a bit further?” 

“Yes. I’m sure.” 

Dean left Sam alone to get ready. When Sam came out, Dean was sitting on the bed, a chair pulled out for Sam. Sam grabbed the stocking and rolled it down, slipping it on. He placed his foot on the chair and slowly rolled it up. He did the same with the other one and then slipped the heels on. 

“Show me” Dean said gently. Sam turned around and showed him the butt plug. “Such a good boy. Now, stay there.”

Dean reached into a bag and pulled out elbow length black satin gloves. He walked over to Sam and showed them.

“What do you think?” Dean asked seriously.

“I want to wear them.” Sam nodded.

“Okay, ask.”

“Please, Dean, your pretty princess wants to wear those gloves.” Sam whimpered and Dean handed them to him. Sam put them on and Dean smiled, cupping his brothers face.

“Do you really want to please me?” 

“Yes” Sam whispered.

“Sit at the table.” 

Sam sat down and Dean reached into the bag and pulled out bright red lipstick. Sam gasped and looked at Dean wide eyed. 

“I wanted to paint your pretty lips, sweetheart. But if this is too much, I can put it away” Sam stays silent for a moment before speaking.

“Please, Dean. Make me pretty” Sam whimpers.

“You’re already pretty, sweetheart.” Sam blushed.

Dean opened the lipstick and Sam parted his lips. Dean applied it and set it down. He had Sam stand up. His baby brother was absolutely stunning. Black satin panties, fishnet stockings, heels, black satin elbow length gloves and bright red lipstick. 

“Have a look in the mirror, beautiful” Dean encouraged. 

Sam walked to the full length mirror and gasped. He started to tear up a bit.

“Dean, this is perfect. Thank you.”

“You’re welcome, princess.”

“I’m your pretty princess.” He whispered to himself. Touching the gloves to his face. “Dean?” Sam whispered. Dean came over and rubbed a hand on Sam’s back. 

“Yeah, sweetheart.” Sam blushed. “Come on, you can tell me” Dean coaxed. 

“Ca-Can you. Can you lock my cock back up?” Dean kissed his shoulder.

“Of course I can.” Sam turned to face Dean. Dean kissed his brother. 

“Dean, I want to be your pretty princess.” 

“Yeah? Do you want to be my pretty princess?” Dean rubbed Sam’s cheek with his thumb. Sam looked down. “Do you want to be my good boy?”

“Castiel is your good boy. I-I want to be your…” Sam shut his eyes tight. 

“Good girl?” Dean finished and Sam nodded. 

“When I’m dressed like this.” Sam whimpered. Dean smirked and nodded.

“Okay, Sammy. You can be my good girl”


	4. Chapter 4

Before Dean put the cage back on Sam, he had him go to the bathroom once more.

“Did you go to the bathroom?” Dean asked Sam.

“Yes” Sam said. 

“Good. Now, let me lock you up, with the sound.” Dean said.

Dean slipped on latex gloves. Sam laid down on the bed and pulled the satin panties down around Sam’s ankles. Dean grabbed stuck the syringe of lube in Sam’s tip.

“Mmmm” Sam gripped the sheets.

“I’m sorry, sweetheart” Dean said sympathetically. 

He placed the cock cage on and slid the sound in, attaching the ball. Dean took his gloves off and pulled the panties back up. 

“That’s better, isn’t it princess?” he cooed and Sam nodded. “Sweetheart, we need to have a little talk.” 

Dean took Sam’s hand and he sat on the chair guiding Sam to straddle him, facing each other. Sam looked worried and Dean kissed his forehead. 

“Now, as you know, Castiel is my good boy and we have a very special relationship. We’ve been dating for two years. Sweetheart, I am so happy that you told me about your kink and what you want. Hunting is a very stressful job” Sam nodded. “You were open to the idea of Castiel and I. Would you be willing to move into the bunker with us?”

“Mmmm” Sam whimpered.

“Castiel will not judge you. He sleeps in a cage, just like you. I would like to be a bit of a Dom to both of you.” Dean said Sam’s head was now resting on Dean’s shoulder and he nuzzled into Dean’s neck. “What do you say? Do you want to show Castiel how pretty you are?” 

“Yes” Sam whimpered. Dean ran stroked the younger man’s hair.

“What are you thinking?” he whispered.

“Co-could we have a few more session alone first?” Sam asked looking at Dean.

“Yes princess, we can have some more alone time. Would it be possible for me to tell my good boy about you? How you want to be my good girl.” Sam whimpered, but nodded. He knew that it was the right thing. “Look at me and use your words” Dean soothed. Sam looked at him.

“Yes, Dean. Tell Castiel about how I want to be your good girl. How I’m your pretty princess.” 

“I will sweetheart. Stand up for me.” Sam did. “Mmmm, I wish I could take you out, show the world just how perfect you look. Dance for me.” Sam did. “Good girl.” Sam blushed. “Tell me what you want, sweetheart.”

“Could-could you hold me.” Sam stopped dancing. “Could you hold me in your arms and give me praises” 

“Yes, princess. I can do that.”

Dean and Sam went to the bed and he wrapped his arms around his brother and stroked his hair.

“You’re such a good girl for me. You look so pretty in those panties. Thank you for trusting me with your secret. I love seeing you so happy and embracing your inner you.” Dean looked down when he felt Sam crying a bit. “Such a pretty princess, with your sexy heels and the long satin gloves. Your lips all nice and dolled up. You were so good for me, warming my cock yesterday. You make me proud sweetheart.”

“Thank you” Sam whimpered.

“Oh, you cry, princess. I wont judge, I’ll just hold you.” Sam nodded and cried a little bit more while Dean just held him. “There’s my good girl.” Dean said kissing Sam’s forehead. 

“Dean” Sam whispered, barely audible.

“Yeah, princess.”

“I love you” Dean pulled his brother tight to him.

“I love you too.”


	5. Chapter 5

The weekend was up. Dean placed a soft kiss on Sam’s lips.

“Sammy, we’re going to do this next weakened, okay?”

“Yes, Dean.”

“And I have your permission to tell Castiel?” 

“Yes. Tell him everything.”

“You were so good for me.” Dean said stroking his brother’s cheek.

When Dean got home, he was greeted by Castiel.

“How was your weekend?” the older man asked, kissing Dean.

“It was good. Sam was very good for me” 

“Good.”

“He said I could tell you” Dean smirked a little bit when he saw Castiel’s eyes light up. 

Dean and Castiel went and sat in the living room. He sat across from Castiel and took a deep breath.

“I promise I wont judge” Castiel said.

“I know, but this is very personal for Sammy.” Dean nodded slightly. “I just don’t want you to…think he’s weird or a freak.”

“Dean, I’ve drank your urine that was inside my ass for a while. I promise I wont think your brother is a freak. Dean chuckled a bit and nodded.

“Sammy, he likes to.” Dean paused “He likes to wear satin panties, fishnet stockings and high heels” Castiel’s mouth dropped. Of all the things, that was not what he thought the younger Winchester would like.

“Really?” Castiel said quietly. “I’m not judging, just stunned.”

“Mm hmm.” Dean nodded for confirmation. “He also wore a butt plug. I call him my pretty princess. I had him also wear black elbow length satin gloves and got him in bright red lipstick.”

“You’re an amazing big brother.” Castiel smiled, reaching out a hand and holding Dean’s.

“There’s one more thing, baby. I asked him if we wanted to be my good boy and he said you were my good boy. That when he’s dressed like that, he wants to be my good girl” Castiel smiled softly and kissed Dean.

“And, was he a good girl for you?”

“Yes, a very good girl. He would like a few more alone sessions with me, but when he’s ready, he would like to move in with us.”

“That would be amazing” 

The next weekend Dean was back in the motel with Sam. Dean instructed Sam to go get ready. He told Sam that he wouldn’t put the cage on until later tonight. Dean noticed there was a box on the bed. When Sam walked out he even had the lipstick on.

“There’s my pretty princess.” Dean smiled. He ran his hand up one of the gloves. 

“Daddy” Sam whimpered and then his eyes went wide, realizing what he had said. “I-I. Dean.” Sam started to panic and Dean pulled his brother tight to him and cradled his head. 

“Did you mean to say that?” Dean whispered calmly. He knew their childhood was not an easy one, with their dad not being around much and when he was around, he was harsh.

“I-I-I” Sam stammered.

“Yes or no, sweetheart. Did you mean to call me that? Do you want to call me that?” Dean started to stroke his brother’s hair.

“Yes” Sam got out. 

“Okay.” Dean gently moved Sam’s face to look at his. He saw that Sam had been crying a bit. “Are you daddy’s good girl?” Dean whispered. Sam closed his eyes and Dean placed a gentle kiss on his for head. "Princess?”

“Yes, daddy. I’m your good girl.” Dean kissed Sam softly and held him close.


	6. Chapter 6

Dean placed a kiss on Sam’s forehead.

“Princess, are you going to show me what’s in the box?” Sam nodded. He walked over to the box and opened it. It was a lingerie sheer black babydoll night gown and silk stockings. “These are beautiful, sweetheart.

“I want to be your pretty princess, even at night.” Dean stroked Sam’s cheek.

“Yeah?” Sam nodded. “Do you also want daddy to plug his cum in your ass?” 

“Yes, daddy. I would like that very much.”

“I’ll do that for you, tonight sweetheart. Now, be a good girl and dance for me.” 

Dean pulled a chair out and sat down in the middle of the room. Sam started to dance, more comfortable with this now. He straddled Dean’s leg and rubbed the back of his hand on Dean’s face. Sam moved aroun, so he was behind the chair and ran a hand down Dean’s shirt. Dean turned his head to look at Sam. 

“You’re such a pretty girl for me.” He whispered.

“Is there anything I can do for you?” Sam asked walking around and turning, while swaying. Touching his own face. 

“Mmmm, sweetheart, you’re doing it. Is there something you want?” Sam blushed and slowed down his dancing, nodded. 

“Tell me I’m pretty, daddy. That I’m a good girl.” Dean smiled sweetly and stood up, he grabbed Sam’s hand and cupped Sam’s cheek.

“You are so pretty princess. Such a beautiful girl for daddy. You’re such a good girl for me. Pleasing me, doing what I want. Dancing for. You’re real pretty when you dance for me, sweetheart. You’re a very good girl for daddy.” Sam leaned into Dean’s touch. Dean kissed him. 

“Daddy, I would like to keep dancing for you” Sam whispered and Dean smirked.

“Okay, princess. Keep dancing for me.” Dean sat back down on the chair while Sam kept dancing. 

When it was time for bed, Dean got undressed and looked at Sam, who stood there blushing, still dressed. Sam stepped out of the heels and rolled the fishnet stockings down. He pulled the gloves off and he walked over to Dean.

“Do you want to cum, sweetheart?” he asked and Sam shook his head. “No?”

“No, just want you to fill me up, daddy” Sam said. 

“Okay, put your pretty new silk stockings and your night gown on for daddy.” Sam nodded.

Dean grabbed the lube and slipped on latex gloves. He watched as Sam pulled the stockings up and put the babydoll night gown on. 

“Good girl. One the bed, elbows and knees.” Dean instructed and Sam obeyed. 

Dean stepped up behind his brother and placed his gloved hands on Sam’s hips. He pulled the panties down and rubbed a hand on Sam’s ass.

“Such a pretty ass, sweetheart.”

Sam shuddered when he heard the popping of the cap. Dean eased the plug out of Sam and squirted some lube on Sam’s hole and started to rub circles. With his other hand, Dean started to stroke himself. He started to rub two fingers and slowly pushed them into Sam. Sam let out a little gasp.

“Are you okay, princess? Is daddy hurting you?” Dean asked stilling his fingers. 

“I’m fine, your pretty princess was just surprised.” Sam whimpered.

“Okay, pretty girl”

Dean slid a third finger in Sam and he felt himself growing hard. Dean pulled his fingers out, quickly taking the gloves off and lined up his cock and slowly pushed in. He gripped Sam’s hips and started to slowly move.

“You okay, sweetheart?” Dean asked rubbing a and on Sam’s thigh. 

“Ye-yes.” 

Dean moved a little fast, running his hands through Sam’s hair. He was amazed at the control Sam had. He wasn’t even hard. Dean’s cock twitched inside his brother and he grunted, cumming and spilling into Sam. 

“Th-thank you, daddy” Sam said. Dean placed a kiss on Sam’s back and pulled out, putting the plug back in.

“You’re welcome, princess. Now, be a good girl for daddy and roll over. Need to put your cage on.”

Dean put gloves on and grabbed the cage. He walked over and knelt between Sam’s legs and lifted his soft penis. He started to stroke it a bit.

“Something wrong?” Sam whispered.

“No, nothing is wrong. Does this please you, pretty girl? Do you feel something?” Sam blushed. 

“I’ve had a tough time getting hard.” Dean gave a gentle squeeze to Sam’s balls and his cock twitched a bit. 

“Good. That was a good response, princess. I’m going to lock you up now.” 

Once Dean got Sam in the cage, he pulled the panties back up, took the gloves off and lifted Sam in his arms, pulling the bedsheet down and tucking him in. 

“I’ll be right back.” Dean whispered. Dean grabbed wipes and wiped his cock. He grabbed a fresh wipe and went over to Sam. “Going to wipe your lipstick off.”

“Hmm” Sam whimpered when Dean wiped it off. He threw the wipe away and climbed into bed, pulling Sam close.

“You were such a good girl for me. You look so pretty in your night gown.”

“I wanted to be a pretty girl for daddy” Sam whispered. Dean kissed the top of his brother’s head. 

“What do you say we talk about getting you a bigger plug, would you like that, sweetheart?” Dean whispered and Sam swallowed, but nodded. “You like having me fill you up?”

“Yes, thank you, daddy” Dean pulled Sam close to him. “Did you tell Castiel?”

“Yes I did and he cannot wait to have you live with us. He wants to meet my pretty princess.” He murmured against Sam’s hair.

“I-I am ready. I want to come home with you.” Dean stroked Sam’s hair.

“Okay, princess. You can come home and be with daddy and his good boy.”

**Author's Note:**

> Comments, kudos. Suggestions.
> 
> I will be writing a third one eventually with all three of them
> 
> *secretly wants someone to do a fan art of this...pretty please!*


End file.
